Sailing Fun

I am a single guy now and I have a daughter whom I will call April for the purpose of this story.  April just turned 18 and she has some very attractive friends the same age.  This is a story about one of her friends and some fun we had with her on the waves. One of the hobbies that has always brought our family a lot of fun is sailing.  We have a nice 36 foot sailboat and we try to go sailing as a family as often as possible during the summer months.  When my daughter turned twelve, she met her best friend Sara. They are nearly inseparable. I watched over the years as they both grew in to attractive young ladies. Both girls are about 5'5 and around 110 pounds. April has brown hair that comes just past her shoulders and brown eyes like her mother. Sara has light brown, almost sandy blonde hair that is slightly curly and beautiful blue eyes. Sara also has a slightly rounder face than April and a slightly larger chest, April being a small 34B and Sara being a 36C. Both girls enjoy playing sports and swimming which keeps them both in amazing shape. As a practice, we try to go sailing most weekends during the summer. Naturally, April usually asks if Sara could come along and I always agree.  Over the years, Sara has fit in nicely and became like part of the family. Most days, it would just be a day sail, leaving in the morning and come back in the evening. Usually a couple of times a summer, we would anchor out and spend the night. Now, sailing with two teenage girls was a lot like sailing alone.  Shortly after leaving the docks, the girls would plant themselves on the foredeck and commence to sunning themselves in their bikinis. Around lunchtime they would come back to the cockpit and we'd eat lunch; then, they would return to the foredeck and continue tanning. I didn't really mind much. After all, I got to go sailing and every time I looked forward, I was greeted with the site of two beautiful young figures (even if one was my daughter). On our fifth trip of the summer with just the three of us, April had asked if we could anchor out by a favorite island.  It was a small island that had one good holding area big enough for one boat and a few rocks that jutted out over the water to jump off of. Usually when we anchored there we were pretty secluded and rarely saw any other boats. I agreed and we loaded up the boat and headed out to the island. As usual, once the sails were set, the girls proceeded to the foredeck and commenced tanning. After about an hour, my daughter walked back to the cockpit and sat next to me. I knew she had something on her mind.  She almost seemed a little embarrassed then asked if it would be ok if they tanned topless. Then she proceeded to explain how they didn't want the tan lines and the other girls at school did and so on. To tell you the truth, I didn't really care. I knew that a lot of girls did it. I told them that they could only do it if we were away from other boaters and they would have to cover up if another boat came by.  April quickly agreed, gave me a quick hug and went back to Sara. I watched as April told Sara the news then each untied their bikini tops and lay down on their backs. I don't think I was really ready for the scenery now present on my deck. I always had a sight of the girls tanning, but now as I looked forward I was presented with two sets of breasts. Two very perky sets of breasts. From my vantage point I could clearly make out Sara’s wonderful breasts and in the cool breeze I could swear I could see two very hard nipples. I snapped out of my stare and said to myself "What are you doing?" I tried to busy myself with checking sails, our course and watching out for other boats. We reached the island around and I lowered the sails. The girls quickly replaced their tops and April helped anchor the boat.  Once secure, we made a light lunch of cheeses, fruit, crackers and veggies. The girls continued to chat about school, other friends, clothes, etc. I personally couldn't help but stare at Sara's chest and I could see her nipples under her bikini top. After lunch, the girls jumped in to the water and swam to the island to jump off the rocks and swim around. I took a jump in the water myself to cool off.  I enjoyed the water and then saw that the girls were swimming back to the boat.  They said they were cold and were going to go warm up. I watched as they climbed the ladder and the water made their suits cling to their tight little bodies. I swam away from the boat a little to try to clear my head. I decided to swim toward the bow of the boat and just float. I floated for a little bit, but the cool water was starting to set a chill in me as well. As I turned over to start swimming, I happened to see the girls sitting on the deck and removing their tops. There were those lovely young breasts defying gravity before me. The girls continued to sun themselves, then they came back and we all talked until dinner time. I almost thought it seemed as though Sara was constantly looking at me with that cute smile of hers. After dinner, the girls did the dishes. I sat in the cockpit and enjoyed the relative silence off it all, meaning over the sounds of the girls below. Around 8PM, both girls came up on deck and we all relaxed. Sara commented on how peaceful and beautiful it was and thanked me for bringing her. Around 9PM, the girls went below to get ready for bed. I did one last check of the anchor and decided to head to bed myself. As I descended the stairs, Sara came out of the forward cabin in just a large t-shirt and who knows what underneath. Though I could tell she wasn't wearing a bra as her nipples were very noticeable through the thin fabric. She quickly slipped in to the head and my daughter came out next in her tank top and shorts to wait her turn. April thanked me again for bringing them to the island and for everything today. I gave her a hug and a kiss on the forehead then watch as Sara come out of the head and April went in. I swear Sara did an extra wiggle. After the girls were in their cabin, I shut down the lights and went to the head myself. I climbed in to the berth in the aft cabin and did my best to try to sleep. I could still hear some giggling and light chatting from the girls. And every time I closed my eyes, all I could see were their succulent breasts. As much as I tried, the only thing that was happening was an erection. I slowly stroked myself thinking of Sara until I released my tension. Then I let the rocking of the boat lull me to sleep. The next morning, I enjoyed my coffee in the cockpit until the girls woke up. Then we had a nice breakfast, a quick swim then weighed anchor to head for home. The following trip was the three of us again and as soon as we left the breakwater, the girls looked at me and said, "Middle of the lake?"  I couldn't help but chuckle and pointed the boat toward open water. The girls quickly took their positions and waited until we were away from other boaters to remove their tops.  This went on through the remainder of July. The second weekend in August went a little different though. The girls were tanning topless as usual on the deck. After a few minutes, my daughter put on her tank top and came back to the cockpit. I could tell she had something on her mind again. This was similar to when she asked about the topless request. "Dad, do you think it would be OK if we tanned nude?" I was taken back a little by the request. Topless was one thing, but nude? I know I am pretty open minded and have sailed nude myself, but the girls? After a couple more minutes of pleading and those puppy dog eyes I relented.  She thanked me and gave me a quick hug then moved back up to the foredeck.  I watched over the cabin sole as the girls sat on their towels and removed their tops and bottoms.  I felt a little relief as the girls laid down on their stomachs. It wouldn't be as apparent if a boat did happen to cruise by. Even from my location it wasn't that noticeable they were naked. As normal I kept a vigil out for other boats and did my best to keep the sails from blocking their sun. We sailed for about an hour and I hadn't really given the girls much thought. I tended to the sails and just enjoyed the feel of the waves and wind. I was getting a little thirsty and decided the girls might be also. So, I hoped below deck to get some drinks. I peered over the cabin again to see the girls still on their stomachs. I took a quick pee in the head and grabbed a soda for myself and two for the girls. I came back up in to the cockpit and put mine in the cup holder than walked forward. A beautiful spinnaker caught my attention as I moved forward and left me totally unprepared for what I was about to see. When I turned back I found the girls had repositioned themselves while I was below deck. Now I had two young ladies laying on their backs in full glory! I stood there for a minute mesmerized by the view of the sun on their slightly tanned bodies, their perky breasts, hardened nipples, the trimmed triangle of hair between my daughter’s legs and the small strip of hair trimmed between Sara’s all framed by the tan lines from their bikini bottoms. I felt a slight guilt as I became aware of blood rushing to my groin. The boat lunged a little and snapped me back to reality. I shook my head to clear it, took a deep breath and continued on. I cleared my throat in a loud manner to alert the girls to my presence. "I brought you some drinks" I said as nonchalantly as I could muster.  My daughter jumped a little bit and sat up, pulling her legs up to her cover up a little. She seemed a little embarrassed. Sara put her hand up to block the sun from her eyes and just smiled and said thanks as she slowly rolled on to her side to cover up and took the drink. I slowly stumbled back to the cockpit and sat down. I could see the girls on the foredeck talking and giggling. Occasionally they would look back my way. Who knew what they were talking about? I hope they didn't see the rising I had in my shorts. I sat in the cockpit trying to will my erection to subside. I just couldn't get the image of those naked bodies out of my head. At lunchtime the girls put back on their suits and joined me in the cockpit. I apologized for walking up there like that. I explained how I thought they were still on their stomachs. April said it wasn't any big deal. I had just surprised her and that I had seen her naked when she was younger. Sara just smiled and it wasn't any big deal to her either. She figured when they asked to tan naked most likely I would see them. We continued to eat lunch and the girls chatted. After lunch we turned the boat around and headed home. We still had a few hours of sailing ahead of us so the girls returned to their sun worshiping. As they peeled off their suits again images raced through my head again and I felt the familiar rise in my shorts. I couldn't stand the pressure this time. I set the autopilot and retreated below deck to my cabin where I proceeded to stroke myself to a fairly quick orgasm. Returning to the cockpit I felt a little better for the rest of the trip home, though I could still see their naked forms as I peered forward. A few weeks later, April was having Sara over for a sleepover.  The girls told me that they wanted to take the boat out the following weekend and asked me if we could.  Of course, I agreed. That weekend came and it was a beautiful day. The sun was out with only a few white puffy clouds. The winds were about 20 knots and it was 85 degrees. I drove up to the docks at 8AM like I normally do. I took a little time to wash down the deck and clear off some of the cobwebs that accumulate over the week. I started up the old iron genny in preparation to head out and went below to stow the sail cover and get something to drink for the voyage. I had just reached in to the fridge when I thought I heard a voice over the sound of the motor. "Ahoy, Cap'n!" came a familiar voice. I climbed up in to the cockpit and standing there on the dock was Sara. She had on her normal blue jean shorts, tank top with bikini underneath and her beach bag over her shoulder. I was a little confused to say the least. "Sara? What are you doing here? April isn't here today." "I know" she replied. "She had a project that she needed to finish and told me to just go with you.  I thought you might enjoy some company today." "Umm, I don't know...", I started. "Come on, I've already told my mom I was going and she dropped me off and she is gone now." I was a little leery at first, but what was I going to do, leave her stranded here until I got back? I agreed and she quickly hoped on board. She told me that she had told her mom that we were staying on the boat last night, and since she had dance class Friday night she was to meet up here Saturday morning. I was still a little upset about her lying to her mother, but the idea of company did sound good. It would almost be like having April on board. After putting her bag below she helped me untie the lines and we motored out of the slip. "Is it like driving a car?" Sara asked? "Huh?" It took me a second to realize what she was talking about. In all the times having her with us, Sara and April always did their own thing. Sara had never really helped out with the boat. "It's pretty similar if not a little easier; less things to hit." I joked. "Can I try?" she asked I stepped aside and let her take the wheel. I gave her some instructions on the rules of the road with other boats and we headed out of the marina. It was nice having someone steer while I took care of the sails and before long we were gliding through the waves under wind alone. I tried to teach her a little about sailing and I tried to talk with her about her plans for next year, working and what my limited teen subject matter would allow. After about twenty minutes, she asked if I would take the wheel. Instead, I showed her how to set the autopilot. Sara went below deck and disappeared in to the head. When she came out, I could see her below deck taking off her tank top and shorts and emerge back in to the cockpit in her little bikini. I watched her lay down on the bench opposite me and stretched out in the sun. I laughed slightly. She looked at me confused. I explained how this is the longest I think she's been on my boat without retreating to the foredeck to tan. "Well, it's not the same without April here, you know. Besides there is plenty of sun back here and the cushion feels more comfortable." I couldn't argue with that. We sailed on for a little longer and I tacked to a new heading. I instinctually moved to the raised side where Sara was laying. Wow, she was beautiful. She was laying there on her back, one arm behind her head, the other laying down by her side. On leg was straight on the cushioned bench and the other arched over the back of the seat giving me a view of a wonderful little camel toe. Again, I felt a little ashamed as I felt a pulse jump in my groin. I did my best to look elsewhere. After a little bit, Sara sat up and looked around. Then she turned to me. "Mr. K, would you mind if I tanned like normal?" she asked. My mind was screaming "NO! Turn around! Head home!" But that other voice inside me won out and what I said was "Sure, if you want to..." With that, I watched as she undid her top and let it fall to the floor. Another pulse shot through my growing cock. Then, she pulled her bottoms off and let them fall. As she resumed her position I now had a sight of heaven. Not only were there two perky breasts, but her legs parted allowing me to see all of her heavenly glory. I tried my best to keep my mind and eyes on sailing. Then I noticed her hand move. She slowly moved her hand up along her shoulder, down softly over her breast to a wind hardened nipple. I swear she gave it a pinch.  Then, she slowly moved her hand down her stomach and along her outstretched leg. My mind was foggy. I was mesmerized. This couldn't be happening. It had to be a daydream...my own perverted daydream. Then Sara sat up and looked at me. "Mr. K?" she asked.   Sara gave me a coy smile and said, "This might seem a little strange, but it feels kind of weird being the only one naked." I took a sad but relieved sigh, thinking she would be getting dressed and lessening the tension. "Would you be naked too?" I freaked and replied, "I don't know Sara." I replied, trying to think of a good excuse. "It's OK, Mr. K. I've seen guys naked before. And besides, I would feel better not being the only one." Sure I thought, but how would I explain the hard on between my legs? Time to head home, get back to the docks! My mind was sending up flags all over the place. Common sense would be to run for home. But common sense didn't win. "OK, just this once" I told her. I still wasn't sure how to explain my erection. I decided to tack the boat again so I could be on the opposite side of the cockpit. That way I wasn't staring straight at her slit. After the tack, I moved to the opposite bench. I tried to think of anything to decrease the blood flow to my cock. Sara sat there staring at me, as if waiting to see if I could go through with it. I finally took a large breath and removed my shirt and shorts. My cock had subsided a small amount, but still pretty rigid. Sara seemed to smile and all I heard was "Nice!" Then she layed back on the bench and returned to her tanning. It was hard to tell but I almost felt as if she was looking at me through her squinted eyes. I placed my arm over my erection, trying my best to hide it. We sailed for a few more minutes and I was working hard on easing my erection when I noticed Sara's hand softly caressing her shoulder, then her breasts again. I thought I would try something else to get my mind off of this desirable girl laying naked only a few feet from me. "Sara, would you like something to drink?" Sara sat up and looked at me. "Sure, I'll get it." And with that she popped below deck. I could see her beautiful naked figure in the galley fishing two sodas from the cooler. She returned to the cockpit in all her glory, two sodas in hand. She put one in the cup holder near the wheel and then stretched out her hand to give me the other. I took it from her and she sat down next to me. Her feet folded sideways under her, leaning toward me on her arm. "You know, you look better than I imagined you would." she confessed. "Excuse me? Imagined I would?" I stated in my own confused way. "I've tried to imagine what you would look like since that first time you walked up on us naked." Each word seemed to not only cloud my mind more but send a new pulse of blood to my growing erection. "And reality looks better than my fantasies". Fantasies? This was really too much to take in. Then she proceeded to tell me how me seeing her naked when we sailed had been a turn on for her. And how she had spent many nights fantasizing about how I looked naked and masturbating to what it might be like to be touched and kissed by me. I was truly in disbelief. My head was spinning and my erections beyond hiding. "I noticed you watching me today and I liked it. I really want you to touch me." There was almost a begging in her voice. I looked at her with all intent on telling her we need to stop and head home. But as I turned, I saw a yearning in her eyes, she moved close to me and before I knew it, our lips met. We kissed, our lips caressed, our tongues played. I moved my hand down around her back and my other hand found her firm breast. I squeezed and I heard her moan through our kiss. I took her nipple between my fingers, amazed at the feeling. Then I felt a soft hand wrap around my cock. I broke our kiss long enough to look down and see her hand slowly stroking me. I too let out a sigh of pleasure and returned to our kiss. It was Sara that broke our kiss next. "There's something I've been fantasizing about doing for a long time now." And with that she moved me legs apart and lowered herself in to the floor of the cockpit. I watched as this beautiful young woman stroked me, her eyes fixated on my erection. Then she lowered herself and took me in to her mouth. I moaned out loud as my head sank back and my eyes closed. I slowly rolled my head around and looked down to see her peering up at me with those blue eyes. My cock was sliding in and out of her mouth and her hand was stroking me. "God that feels great!" was all I could muster along with another moan. And with that, she lowered her head and continued her sucking, bobbing and stroking. I watched as she wonderfully pleasured my shaft and used her free hand to squeeze and play with her nipples. I felt the growing eruption flowing as my breath quickened. I felt her sucking and stroking quicken as well. I began to moan louder and managed to get out an "I'm gonna...” before I exploded in her mouth. She stopped her head bobbing and slowly stroked and sucked all of the juices out of me. I sat there in a state of limbo. The reality of what had just happened, the pleasure of it all. Shortly thereafter, Sara moved up, still holding my cock in her hand. She came up to me and we kissed some more. I knew what I should have done, but I also knew I wanted to repay her for the pleasure she had just given me. Wrong or not, I knew what I was going to do. I slowly laid Sara down on the cushion in the cockpit. I made a quick look around. The winds had lighted and other boats were nearby. I lowered my lips and kissed hers again. Then I slowly moved over to her neck and down her shoulder.  I had been longing myself to feel her nipple against my tongue. I felt it enter my mouth and I licked and sucked. I heard her let out a moan and felt her fingers run through my hair. I let my hands caress her tits and took time to kiss and lick each one. Then I let my lips continue their travels down. I kissed over her ribs and over her stomach. I kissed my way down until I found her little strip of hair she had trimmed. I let my tongue and lips follow her pathway to heaven. Finally, there I was, only inches away from this entrance to paradise. I could see moisture glistening in the sun along her slit. I slowly slid my tongue along her opening, tasting her nectar. She let out a gasp as my tongue slipped along her clit. I let my tongue taunt and tease, open and please. I then took my finger and slowly let it enter her. Sara gave out a loud moan as she pulled my head closer.  As I continued to finger and lick one of her hands left my head. I looked up to see her playing with her nipples again. I could hear her breathing getting deeper and quicker, I arched my finger up inside of her and took her clit in my mouth. And as if on cue, her body tensed, and twitched. I saw her teeth grit and her abs tighten. She let out a guttural "Aaahhhhh", then a loud "Oh Fuck! Oh! Oh! Eeeeeyyyyaaahhh!!!". Then a louder moan as her fingers dug in to my skull and gripped my hair.  I made very small movements with me tongue and fingers as her body twitched several more times. "Oh my God! Oh my God! I can't... I can't..." she panted. I then moved up and we locked in a heated kiss. When we separated, she looked at me. "Better than your fantasy?", I asked. Sara got a big grin on her face almost laughing. Sara looked down and saw my semi rigid cock. "Looks like you need more attention," I noticed that we were pretty far out in the lake. So, I quickly turned us toward home and adjusted the sails to keep us on course but at a pretty slow pace. There weren't any other boaters around so I knew we'd be safe for a while. Then I took Sara by the hand and led her below deck. I led her in to the V-berth where she and my daughter had slept only weeks before. I pulled her on to the bed with me and we kissed. Sara naturally took my cock in her hand and slowly stroked it while we kissed. I caressed her breasts and body as I felt more blood entering my cock. Sara then moved herself down and took me back in her mouth. Her talented tongue made me moan more as I grew hard again. I knew this time I didn't want just a blow job. I pulled her up and positioned her on her back. Then I raised myself between her legs with my cock pulsing before her entrance. I looked down at her and she was looking between our legs. Then she looked up at me with a shy, innocent look and nodded. I leaned down and kissed her lips. Then I slowly began thrusting forward. I could feel the tightness of her. I felt every bit as my head entered her. I moved slightly forward allowing more to enter her. I worked slowly back and forth, only inching in until I felt a barrier. Her virginity? I stopped and looked back at her. She was slightly biting her lower lip. God she looked sexy! She looked back at me and nodded again. "Are you sure?" I asked. She smiled and nodded, saying, "I've wanted you to be my first for almost a year now.  I started on the pill just after Christmas, so when you're ready, just go ahead and finish inside me.  I want all of you." I lowered my lips to barely touch hers. I slowly started sliding in and out of her again, each time stopping at her barrier. Then in one thrust I broke through. Sara's nails gripped my shoulders and I heard a whimper. I laid there inside of her until she relaxed. "Are you OK?” "Yes, it just hurt a little bit", she said, then gave me a little grin. I kissed her once again and started to slowly side in and out of her. I delighted in hearing small moans of pleasure in my ear. I moved more, deeper. I wanted so badly to fuck this girl. AS I continued, her moans became louder. I could feel her nails along my back and ass pulling at me. I knew I wouldn't last too much longer. I heard her start to grunt "Yes, yes!" I watched as pleasure raced across her face, her mouth open, moans exiting. She looked at me as if she were afraid of what was about to come, or in this case, cum. I thrusted a few more times and felt my own eruption coming on again. My moans increased and this seemed to stir her on. "Yes... yes... oh... cum...in...me..." she huffed and gasped. I couldn't hold back anymore. It was too much. I felt my cock swell, my balls release. A loud moan from Sara as her nail dug in to my back. I exploded inside of her. My first shot caused her to dig her nail across my back as her own orgasm ensued. I felt myself release four or five more times inside of her before I dropped on the bed, spent. Sara continued to grip me, breathing heavy and letting out small whimpers. Finally I moved a bit more and my cock slipped from between her legs. I rolled over on the bed and looked down. There was a glistening of pink from my cum and her virginity. Sara rolled over and put her hand on my sweaty chest. Under heavy breathing she uttered, "That was amazing! I mean...." "Yes it was, thanks to you." I replied. With that I gave her a kiss on the forehead and then more deeply on her mouth, then our tongues entwined.   She laid there for another minute then sat up. More of my juices flowed from within her. Sara looked down at it then over at me and laughed. "I guess we should clean that up before April and I sleep here again?" "Probably so", I replied. With that we slid off the berth and pulled the sheets off. Sara went to the head to clean up some. I used the sheet to wipe myself off and went up to the cockpit. I surveyed the area noting where any boats were, and then pulled on my shorts. I pulled in the sheets and the boat took hold of the winds. Sara joined me in the cockpit and put back on her bikini. I was a little sad to see her cover her beautiful body, but it would be best since we would be near other boaters soon. Sara snuggled in my arms for the remaining sail home. "Thanks for being my first, Mr. K", she said. "That pleasure was truly all mine", I replied. "I don't think so.  That was pretty fucking great...", Sara said.  And it certainly was great.   The following weekend we found out that Sara's parents were getting a divorce and her mother was going to be moving with her out of state at the end of summer. Just before school started, April and I said goodbye to Sara and her mother. My daughter was very sad at losing her friend. I too was sad, for my own personal reasons. Sara said she was hoping to come back the following year for college and maybe some more sailing.  I told her that she was welcome anytime.   I hugged my daughter against me as we watched them drive away.  April asked me, "So, when she comes home from college, can I watch you guys do it on the boat, Daddy?"  I nearly fell over.  April laughed and I just nodded and smiled.  "We will see....", I said.